Radiation-sensitive resin composition

Abstract

1. A radiation-sensitive resin composition comprising: (A) a resin insoluble or scarcely soluble in alkali, but becomes alkali soluble by the action of an acid and (B) a photoacid generator. The resin comprises (a) at least one recurring unit of the following formula (1-1) or (1-2), and (b) at least one recurring unit for the following formula (2-1), (2-2), or (2-3).

1. A radiation-sensitive resin composition comprising:
 (A) a resin insoluble or scarcely soluble in alkali but which becomes alkali soluble by the action of an acid, comprising: 
 a recurring unit (1-1) shown in the following formula (1), 
 
       
         
           
           
               
               
           
         
       
       wherein
 R  1  represents a hydrogen atom or a methyl group; 
 A  1  represents a single bond or a group -X 1 -COO- wherein X 1  represents a methylene group, a linear or branched alkylene group having 10 or less carbon atoms, or a bridged or non-bridged divalent alicyclic hydrocarbon group having 10 or less carbon atoms; 
 each R 2  individually represents a linear or branched alkyl group having 1-6 carbon atoms; 
 R 3  represents a hydrogen atom, a linear or branched alkyl group having 1-6 carbon atoms, or a linear or branched oxygen-containing organic group having 1-6 carbon atoms; 
 n is 0 or 1; and 
 at least one recurring unit having a lactone skeleton selected from the group consisting of a recurring unit (2-2) and a recurring unit (2-3) shown in the following formula (2), 
 
       
         
           
           
               
               
           
         
       
       wherein:
 R 8  represents a hydrogen atom or a methyl group; 
 B is a methylene group, an oxygen atom, or a sulfur atom; 
 R 9  represents a hydrogen atom, a linear or branched alkyl group having 1-6 carbon atoms, or a linear or branched oxygen-containing organic group having 1-6 carbon atoms; 
 R 10  represents a hydrogen atom or a methyl group; and 
 R 11  represents a hydrogen atom, a linear or branched alkyl group having 1-6 carbon atoms, or a linear or branched oxygen-containing organic group having 1-6 carbon atoms, and 
 (B) 1-(4-n-butoxynaphthalen-1-yl)tetrahydrothiophenium nonafluoro-n-butanesulfonate as a photoacid generator; 
 wherein the resin (A) further comprises a recurring unit of the following formula (3): 
 
       
         
           
           
               
               
           
         
       
       wherein R 12  represents a hydrogen atom or a methyl group, Y indicates a hydrocarbon group with a valence m having 12 or less carbon atoms that may be substituted with fluorine atoms, D represents a polar group having a valence (m- 1 ), and m is 2 or 3. 
     
     
       2. The radiation-sensitive resin composition according to  claim 1  further comprising an acid diffusion controller. 
     
     
       3. A radiation-sensitive resin composition comprising:
 (Al) a resin, which is insoluble or scarcely soluble in alkali, but becomes alkali soluble by the action of an acid, comprising a recurring unit represented by formula (1-1) 
 
       
         
           
           
               
               
           
         
       
       wherein:
 R 1  represents a hydrogen atom or a methyl group; 
 A 1  represents a single bond or a group -X 1 -COO- wherein X 1  represents a methylene group, a linear or branched alkylene group having 10 or less carbon atoms, or a bridged or non-bridged divalent alicyclic hydrocarbon group having 10 or less carbon atoms; 
 each R 2  individually represents a linear or branched alkyl group having 1-6 carbon atoms; 
 R 3  represents a hydrogen atom, a linear or branched alkyl group having 1-6 carbon atoms, or a linear or branched oxygen-containing organic group having 1-6 carbon atoms; and n is 0 or 1, 
 and at least one recurring unit having a lactone skeleton selected from the group consisting of the recurring unit (2-2) and the recurring unit (2-3) shown in the following formula (2), 
 
       
         
           
           
               
               
           
         
       
       wherein:
 R 8  represents a hydrogen atom or a methyl group; 
 B is a methylene group, an oxygen atom, or a sulfur atom; 
 R 9  represents a hydrogen atom, a linear or branched alkyl group having 1-6 carbon atoms, or a linear or branched oxygen-containing organic group having 1-6 carbon atoms; R 10  represents a hydrogen atom or a methyl group; and R 11  represents a hydrogen atom, a linear or branched alkyl group having 1-6 carbon atoms, or a linear or branched oxygen-containing organic group having 1-6 carbon atoms; and (B) 1-(4-n-butoxynaphthalen-1-yl)tetrahydrothiophenium nonafluoro-n-butanesulfonate 
 
     
     
       4. The radiation-sensitive resin composition according to  claim 3 , wherein the content of the recurring unit (1-1) in the resin (A- 1 ) is 10-80 mol% and the total content of the recurring unit (2-2) and the recurring unit (2-3) in the resin (A- 1 ) is 20-80 mol%. 
     
     
       5. The radiation-sensitive resin composition according to  claim 3 , wherein the amount of the photoacid generator is 0.1-20 parts by weight for 100 parts by weight of the resin (Al). 
     
     
       6. The radiation-sensitive resin composition according to  claim 3 , further comprising an acid diffusion controller. 
     
     
       7. The radiation-sensitive resin composition according to  claim 3 , further comprising a solvent in which the resin (Al) and the photoacid generator are dissolved to form a solution with a total solid content of 5-50 wt% 
     
     
       8. The radiation-sensitive resin composition according to  claim 7 , wherein the solvent comprises at least one solvent selected from the group consisting of a linear or branched ketone, cyclic ketone, propylene glycol monoalkyl ether acetate, alkyl 2-hydroxypropionate, alkyl 3-alkoxypropionate, and y-butyrolactone. 
     
     
       9. A radiation-sensitive resin composition comprising:
 (A) a resin insoluble or scarcely soluble in alkali, but becomes alkali soluble by the action of an acid, comprising: 
 a recurring unit (1-1) shown in the following formula (1), 
 
       
         
           
           
               
               
           
         
       
       wherein R 1  represents a hydrogen atom or a methyl group, A 1  represents a single bond or a group -X 1 -COO-, wherein X 1  represents a methylene group, a linear or branched alkylene group having 10 or less carbon atoms, or a bridged or non-bridged divalent alicyclic hydrocarbon group having 10 or less carbon atoms, R 2  individually represents a linear or branched alkyl group having 1-6 carbon atoms, R 3  represents a hydrogen atom, a linear or branched alkyl group having 1-6 carbon atoms, or a linear or branched oxygen-containing organic group having 1-6 carbon atoms, n is 0 or 1,
 a recurring unit (2-1) of the following formula, 
 
       
         
           
           
               
               
           
         
       
       wherein R 6  represents a hydrogen atom or a methyl group, A 3  represents a single bond or a group -X 3 -COO-, wherein X 3  represents a methylene group, a linear or branched alkylene group having 10 or less carbon atoms, or a bridged or non-bridged divalent alicyclic hydrocarbon group having 10 or less carbon atoms, R 7  indicates a linear or branched alkyl group having 1-6 carbon atoms or a linear or branched oxygen-containing organic group having 1-6 carbon atoms, two or more groups, if present, being either the same or different, i is an integer of 0-4,j is 0 or 1, k is an integer of 1-3, and
 a recurring unit (2-2) of the following formula, 
 
       
         
           
           
               
               
           
         
       
       wherein R 8  represents a hydrogen atom or a methyl group, B is a methylene group, an oxygen atom, or a sulfur atom, R 9  represents a hydrogen atom, a linear or branched alkyl group having 1-6 carbon atoms, or a linear or branched oxygen-containing organic group having 1-6 carbon atoms, and
 (B) 1-(4-n-butoxynaphthalen-1-yl)tetrahydrothiophenium nonafluoro-n-butanesulfonate as a photoacid generator. 
 
     
     
       10. The radiation-sensitive resin composition according to  claim 9 , further comprising an acid diffusion controller.